Acetic Anhydride → HCID 50991461, compound

HRID 2192265Notes

Reaction equation

HRID 2192265 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][N:9]([CH3:41])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:27]3[C:22](=[CH:23][C:24]([C:28]4[CH:29]=[C:30]([NH2:34])[CH:31]=[CH:32][CH:33]=4)=[CH:25][CH:26]=3)[N:21]([C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)[CH:20]=2)=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:8][N:9]([CH3:41])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:27]3[C:22](=[CH:23][C:24]([C:28]4[CH:29]=[C:30]([NH:34][C:1](=[O:3])[CH3:2])[CH:31]=[CH:32][CH:33]=4)=[CH:25][CH:26]=3)[N:21]([C:35]3[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=3)[CH:20]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 50991733HCID 50991733, compound

Product 1

HCID 50991461HCID 50991461, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (4.8 μL, 0.5.1 μmol) was added to a mixture solution of 3-(3-(4-(2-(dimethylamino)ethoxy)phenyl)-1-(pyridin-4-yl)-1H-indol-6-yl)benzenamine (2.2 mg, 4.9 μmol) in pyridine (0.4 mL) at room temperature. After stirring for 15 hours at room temperature, the reaction solution was added to saturated sodium bicarbonate aqueous solution and then extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (preparative TLC, DCM:MeOH=10:1). The target compound (1.5 mg) was obtained as white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. customThe residue was purified by chromatography (preparative TLC, DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-2a61ae21bf1a4a70bf3a7af1df607f98
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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